


Sloppy Seconds

by Anonymous



Category: Supernatural
Genre: Barebacking, Bottom Dean, Breathplay, Casual Sex, Cock Slut Dean Winchester, Condoms, Deepthroating, Dom/sub Undertones, Double Penetration, Face-Fucking, Gangbang, Inspired by GIFs, M/M, Multiple Orgasms, Outdoor Sex, Overstimulation, Painplay, Plot What Plot/Porn Without Plot, Public Sex, Rough Sex, Sort Of, Stranger Sex, Strap-Ons, dean just loves sex and has it a lot
Language: English
Status: Completed
Published: 2018-04-23
Updated: 2018-04-23
Packaged: 2019-04-26 20:40:54
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 10,865
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14410158
Author URL: https://archiveofourown.org/
Summary: 5 times Sam gets sloppy seconds and one time he has Dean all for himself. (Or, 11 times Dean has sex.)





	Sloppy Seconds

**Author's Note:**

> The first one is based on a gif, which I'll link right here (it's nsfw): http://secretwincest.tumblr.com/post/139227800536/todaysdirtysecretis-no-words-are-exchanged-no

1.

Dean doesn't have a type, not really. He's happy to fuck whoever no matter what they look like, how they carry themselves, whether they want to be in control or have him control them. He doesn't care if they want to have the plainest vanilla sex or do some kinky shit he's never heard off. He doesn't even care what they have between their legs or whether they're a man or a woman, both, neither. Dean just fucking loves sex, in every shape it comes in. He doesn't have a type, doesn't even really hava a preference, but he does have needs. 

And sometimes, what he really needs is to have his ass pounded until he screams. He has plenty of people in his phone contacts who'd be there if he asked, guys with broad shoulders and big cocks who know exactly what to do with his ass to make him go crazy, clever people with XL strap-ons who make him come so hard he can't think for the next half hour. None of them live anywhere near the tiny less-people-than-cows town in Missouri their last hunt has taken them, though.

So he goes to a bar - or, _the_ bar, since it's the only one in town -, keeps his eye out for guys who don't look at him right. Who look scared when they see someone as pretty has Dean. Who choke on their beer when he winks at them.

Most men at the bar are old. Not hot-old, gross-old, and Dean doesn't even try with any of them. There's only one guy his age. He's drinking with a bunch of the older guys, still in dirty pants and galoshes even though he's wearing a clean shirt. Dean can tell from body language and some bits of conversation he overhears that the man sitting closest to the guy is his father. The guy seems uncomfortable even as he laughs at some vague joke his dad tells.

He might not be interested in pounding Dean's ass. But if he is, he'll make it good. He doesn't seem like he'd have much experience, but he has broad, muscular shoulders and a promising bulge in his pants.

He catches Dean's eye a couple of times, and nods minutely when Dean points his thumb behind him to the door.

He clears his throat. 'I, uh, I'm heading off to bed. Early day tomorrow.'

He gets a couple of slaps on the back and incoherent mumblings in goodbye and walks out the bar, cheeks faintly pink. Dean waits a good five minutes before he follows him, more for the guy's sake than his own. He's been in enough of these small communities to know that they can be terrifying for gay people. He doesn't want to guy to be needlessly paranoid, although Dean knows none of the men will suspect a thing.

He's waiting for Dean a couple of yards away from the bar, deliberately out of the view of any of the windows and in a place where he can easily duck out of sight should anyone come out of the bar. He looks almost shy right now, Dean hopes he won't be the same in the sack.

Dean takes him back to the motel, because Sam is on a Tinder date and Dean still doesn't get any of that shit except that Tinder dates are supposed to end in sex, and Sam's the kind of gentleman who stays the night and everything, so he'll be out of Dean's hair at least until tomorrow.

They're quiet as they undress. The guy has a frantic edge to him, like he wants to get this done before anyone catches them at it. Dean fingers himself open while the guy neatly folds his clothes (because in no matter how much of a hurry he is, it's important that he won't look like he had sex when he walks out of here) and puts on the condom Dean hands him.

Dean gets on his back for him, because the guy is pretty enough to look at and maybe Dean can get some kisses out of him.

The guy does seem shy as he lines his dick up with Dean's hole, waiting as if he isn't ready to do this yet. 

Dean can see the exact moment the guy's shyness melts away and he finally lets go.

The pace he sets is hard, brutal. He doesn't give Dean any time to adjust to his size, just starts pounding away while Dean scrambles at his shoulders weakly and keens with every thrust. He's being fucked hard enough that every thrust pushes him further up the bed and it's the only way he ever wants it. No use in being fucked if it doesn't leave him sore for days. If it doesn't leave him feeling helpless and utterly objectified as the guy chases after his own pleasure without caring about Dean's. Any time be hits Dean's prostate makes Dean wail and whrite on the creaking bed, even if the guy isn't doing it on purpose.

He fists his own cock once the guy starts nearing his orgasm and its all so much, so good, that he barely even notices the door slamming open. It's only when a gun cocks that he startles back to full awareness. That sound could probably wake him from the dead, as attuned as his is to it, as quickly as he reacts to it. A second after the safetly of the gun clicks, the lights flick on.

The guy scrambles off of him, out of him, away, leaving Dean cold and empty. Dean has already grabbed the gun from under his pillow.

The guy is pulling on his clothes with shaking hands, glancing at the person at the door, even though that person has already lowered their gun, put it away, even. 

It's Sam, who isn't even looking at the guy. He's looking at Dean as Dean puts his gun away, too.

Dean's stomach does something weird, a mix of panic and something else that almost pushes him over the edge, almost makes him come right then and there. It's not like Sam doesn't know that Dean needs this every now and then, that when he stays away until the late hours of the night, it isn't just to drink. It's just that they don't talk about this, that they prefer to act like sex is the one normal thing in their lives - straight, vanilla, simple. This is gonna make Sam so uncomfortable and that's just gonna make him act all short and distant.

The guy is fully dressed in seconds and bolts out the door as if his life depends on it. Maybe it does in a place like this.

Sam closes the door as soon as he's gone. Turns the lights back off.

Dean is both exhausted and so high-strung he could burst, so really the fact that he manages to get a blanket over himself is damn near a superhuman feat. He's shaking and sweating and aware of every little piece of the low thread count sheets scraping over his skin. He wants to get a hand on himself, wants to finish this and go to sleep, maybe play with his ass a little before he does, but Sam is right there, eyes trained on Dean even in the dark.

'Take it the date didn't work out?', Dean asks. He's still panting like he just ran a marathon, his cock rock hard, even more so now that the rough sheet is dragging over it with every minute move Dean makes.

'Take it yours did,' Sam says easily, as if he didn't just see his big brother take cock like he was born to do it.

'I don't know if that still counts after he ran out on me.' Fuck it, its dark enough. Dean gets a hand on his cock and squeezes, just to have some relief. It doesn't help much, but it's something.

'Sorry about the gun. You sounded like you were being mauled like a Hellhound. I didn't consider -'

''S fine,' he mumbles. He wants to come so bad. Wants Sam to leave so he can take care of it, even if it won't be the same.

'Did he hurt you? It sounded like he was hurting you.'

'God, Sammy, don't make me talk about this with you. You have the birds and the bees and then sometimes there are bees who enjoy a little bit of pain to go along with their pleasure. It's -'

'That it feels good doesn't mean it can't cause injuries,' Sam interrupts him.

He walks over to the bed, pulls away the sheet and turns on the flashlight on his phone. With his other hand he pushes up Dean's legs, exposing his ass.

Dean can't help the whimper that escapes him when Sam prods at his sore asshole.

This isn't that weird. They check each other for injuries all the time. This isn't any different. 

Or it wouldn't be of Dean wasn't rock hard still.

He squirms a little when Sam's index finger pushes past his rim. 'This is going to be sore,' he says, voice a quiet rasp. 'But none of the skin is broken.'

Dean doesn't say anything in return, although he knows he should make a joke to make this less weird. He's back in the haze he was in before Sam cocked his gun. He's painfully hard, inexplicably aroused and isn't anywhere near as fucked out as he had wanted to be by the end of this night.

Sam goes into the bathroom to wash his hands and Dean slowly gets up.

The dresser is the perfect height for what he wants to do. Low enough for him to rest his hands on it, a couple inches to high for Sam to bend him over the surface. Somehow he isn't disturbed by the crazy idea he just had, isn't disturbed by taking his own brother's cock, but he is bothered by the idea of Sammy bending him over or holding him down. That's not a way for a baby brother to treat his big bro.

As an afterthought, and because Sam always takes his time washing his hands and Dean doesn't have the patience to just stand there while he waits, he grabs the lube and squirts some over his hole, hoping it will look more inviting.

When he hears the bathroom door open, he arches his back a little, pushing out his ass and waits. The bathroom door is behind him, so there's no way for him to gauge Sam's reaction.

His position and the fact that he hasn't put any clothes on are unmistakable, though. And Sam knows that. They're not entirely new to this.

It's been years now, and neither of them ever acknowledged it, not while it was happening and definitely not afterwards, but they've gotten each other off more than once. While sharing the same bed in some cheap motel room, if either of them started to jerk off the other would help him finish. They wouldn't even look at each other while doing it, but they would do it none the less. Sammy always stroked Dean hard and fast, right on the edge of painful while Dean nudged a finger into his own hole. Dean would tug at Sam's hair while stroking Sam though his orgasm, and Sam had to bite his fist to keep their dad from hearing his moans. One time, Sam was jerking Dean's cock and crawled down the bed to lick it. Dean had never come that fast in his life.

So this isn't entirely new, although it's been years since they've done anything sexual. It doesn't surprise him when he feels Sam's hand leaving the barest touch on the small of his back. Dean arches his back a little further, lets his hand drift to his cock to show how much he wants this.

To his surprise, Sam firmly pulls his hand away and sets his back against the dresser. Then there's the sound of a zipper, a condom package, nothing.

Everything is still for a moment and then, slowly, carefully, the head of Sam's cock pushes against Dean's entrance.

He bites his lip and white knuckles the dresser as Sam pushes in, impossibly bigger than the guy who just fucked Dean. It's doesn't really hurt. Dean is loose enough after such a rough fuck, but the stretch still brings tears to his eyes. He's so fucking turned on. If Sammy would let him touch his dick, he'd be coming right now.

Neither of them says a word as Sam slowly, endlessly works his cock in. 

Dean wants to tell him to go faster, but that's not how this works. They don't talk. They don't acknowledge the other.

Sam's hips are pressed against Dean's ass and then he's pulling out again, feels like his dick goes on forever. He pushes back inside for another eternity.

Dean whimpers when he bottoms out again and Sam chases that sound, pulls out and in, pauses, out and in, pauses. Faster and faster as Dean's cries and whimpers get louder.

Then he grips Dean's hips, huge hands envelopping him like he's tiny. And he feels fucking tiny, speared on a cock like that, Sam's huge body behind him, his long fingers squeezing Dean's hips in a way his oversensitive body feels all over.

With his new leverage on Dean's hips, Sam finally starts fucking him like he means it, pulling Dean towards him every time he pushes inside.

Dean is a sweaty, panting mess, so turned on he's verging on delirious. The dresser rattles with every one of Sam's thrusts and and Dean's hands are slipping off the dresser the more he loses control over his muscles, so Sam pushes him fully up against it, almost lifting Dean up with the force of his next trust.

It feels so good Dean could cry. His ass is burning with how much it has taken tonight, Sam isn't touching him anywhere other than his hips, but he's slightly folded over, his legs bent in a way that lets him push _up_ into Dean in a way that pushes Dean up onto his tippy toes. Sam's grip is going to leave bruises, his breath is hot against Dean's neck, his quiet pants the only thing he hears.

It takes him a while to realise he himself has gone quiet, that he's not moaning like a bitch anymore the way he was when the other guy was fucking him. Just breathing is hard enough right now. Sammy effectively fucked his brain out. 

Dean is being fucked on Sam's big cock and taking it like a rag doll.

His orgasm takes him completelyby surprise. One moment he's realising that he really is just taking it like Sammy's little sex toy, that's he's just a hole for his baby brother to fill. He's not even really standing anymore, the dresser and his brother are holding up most of his weight.

The next moment, his come is spurting over the dresser drawers, back arching and ass clenching in a way that makes Sam grunt.

Sammy keeps going, holding Dean up as he chases his own orgasm with hard, stuttering strokes. He squeezes bruises into Dean's hips as he comes. Dean sort of wishes the condom wasn't there, that he could go to bed with Sam's come still in him, but he isn't going to say that out loud. Ever.

Sam stays inside him as he softens, even though Dean can't stop his ass from clenching and unclenching, too fucked out to have much control over his muscles.

Sam only pulls out when Dean can take some of his own weight again. He goes to take a piss in the bathroom while Dean pulls on underwear and crawls into bed, alseep before Sam comes out. 

-

As expected they don't talk about it. Their usual banter and easy silences are just as usual and easy, even when Sam's gaze lingers a little too long on Dean in the days after, every time Dean sits down as carefully as he can, still sore.

 

2.

It's like an itch to Dean, that need to be fucked hard and good. Once he scratches it, it stays away for a good while, but it always comes back in a couple of weeks. Vanilla one night stands can only do so much to satisfy him. Sometimes he just needs something a little stronger. A good cock to fill him up.

This time they've been driving from the east coast to the west coast for some demonic omens that really couldn't wait. They've slept in the car a couple of nights to save on cash and they're probably not going to be stopping anywhere decent until they're in California.

Dean fingered himself in an unexpectedly clean bathroom in Maryland, the dark of night somehow making him crazy enough to think Sam would fuck him again if he was just loose and desperate enough. He forgets about that idea as soon as he's come and can think sane thoughts again, but the lube still comes in handy when the bored guy in the next gas station is openly watching porn and doesn't stop when Dean comes in to pay for a bag of M&M's and a couple bottles of Coke. Sam is alsleep in the passenger seat after driving for the last six hours. Dean has time.

The guy is watching straight porn, but it's anal at least. He could always be one of those guys who doesn't care if it's a guy or a girl's ass, as long as it's an ass.

'You wanna fuck me?', Dean asks, knowing the horniness he hasn't been able to do much about on the road must be driving him crazy, because this is reckless and dangerous and Sam would kill him if he knew about this. He hands the guy a ten.

'What?' The store clerk says, not even looking up at Dean as he hands him his change back.

'My ass is better than porn,' he says, and that finally gets the clerk's attention. His heart is beating like crazy. He's so fucking turned on after being horny and having nothing to do about it for weeks. The guy is sort of hot, and the fact that he's at least a decade older than Dean makes him even hotter.

Dean slowly starts to walk around the cash register. There's only two ways this can go, and he's willing to risk the first option becase the second is so good.

'Ass is an ass,' he says. 'All you need is a condom and you can have it.'

The clerk is slow, reluctant, as if he's expecting all of this to disappear. He glances at the window at the front of the store, seems to decide it's safe at this hour, and then looks at Dean and keeps looking at him as he grabs a box of condoms from the display right at the counter and takes one out. He still looks at Dean as he unzips, takes his cock out and rolls the condom on.

'Come on,' he says, voice raspy and turned on, as his already rock hard cock confirms. 'Where is that ass of yours.'

Dean turns away from him, so he can lean on the counter, and pulls down his pants enough to bare his ass.

He doesn't look behind him, lets the man slamming inside catch him by surprise. He isn't very big, but it's been a couple hours since Dean fingered fimself by now and there's a definite stretch.

Dean revels in the pleasure, the man's hands on his shoulders squeezing painfully, their flesh slapping together with every thrust.

'Come on, come on, harder,' he whines, pitching his voice a little higher because straight guys like it when he sounds like a girl. He tries to moan and cry out like a porn star as the man complies and fucks him harder.

He moves one hand from Dean's shoulder to the back of his neck and pushes, not enough to bend Dean over the counter, but enough for him to feel it. The man is just using him for better leverage to fuck him, without any regard for how it feels for Dean and it turns Dean on like crazy.

He starts jerking his cock hard and fast as he feels the man's rythm stutter. The man comes and pulls out, slapping Dean's ass as Dean furiously jerks himself to completion.

The man hands him a box of tissues and Dean cleans his own come of the counter after he's pulled up his pants. Then he gives the man a nod and leaves with his Cokes and M&M's.

When he gets to the car, Sam is awake. Dean can tell from how dark his eyes are that he saw most of that. Sammy's cock is rock hard, the outline clear inside his pants.

Dean gets in the car and drives away.

Even when he's keeping his eyes on the road, he notices in a few glances that Sam's cock is staying hard, even after ten minutes.

When half an hour passes and it still isn't going down, Dean starts to get a little worked up himself and makes a decision.

He finds a quiet road, then a quiet part of that road and pulls over. In the middle of the night, no one is going to drive by. Even if anyone does, they won't notice them.

Dean gets out of the car and unzips his pants before Sam can say anything. He has a bottle of lube in his pocket that he takes out before he leans against Sam's side of the car. Not over the back or the hood because he doesn't want Sammy to bend him over, so he props one forearm against the top of the car, over the second window, and uses the other to push down his pants and liberally coat his ass with lube. Sam is doing something in the car, and it takes Dean a moment to realise he's looking for a condom. Once he finds one, he gets out of the car, too, and closes the door. Dean drops the lube and braces his other arm against the car, too while Sammy puts on the condom.

Sam pushes at Dean's rim with two fingers to check if he's ready, then slams in without warning. Dean muffles his cry in his arms. Sam puts an arm around his waist and fucks him hard and fast.

Dean's ass is oversensitive and his dick can't get hard so soon after an orgasm, so he tries to commit every part of this to memory so he can jerk off to it some other time.

Sam bites into his shoulder as he lets out these throaty animal grunts. It almost sounds like he's growling.

Dean loves it so much. The pain on his shoulder and around his rim and deep inside his ass as Sam pushes him open, pushes all of Dean out of the way to make room for himself. 

Sam only speeds up as he gets closer to orgasm, squeezing Dean's waist so hard tears spring into his eyes. He cherished the bruises he had from last time, dug his fingers into them every time he jerked off and came harder than he usually did on his own.

Somehow he's quiet again. Just breathes hard as Sammy fucks him good and painful and perfect.

Dean jerks his oversensitive cock just to add another point of pain and chokes out a sob.

Sam's hand covers his on his cock and Sam comes while litterally squeezing sobs and cries out of Dean, who slumps against the car as soon as Sam pulls out. It took Sam less than five minutes to come, which is short compared to his usual stamina (because Dean has grown up listening to his baby brother jerk off). He must have been crazy turned on.

Sam zips up and then pulls Dean's pants back up. He manouvers Dean into the passenger seat because even Dean can admit he can't drive right now.

He's shaky as Sam, fully composed, starts the car and drives away. Dean drifts off to sleep not much later.

 

3.

They take two days off because they just finished a rollercoaster of a hunt, Sam is recovering form a severely sprained ankle and neither of them wants to move on from sunny California just yet.

Sam spends time going to the gym and reading books for fun, while Dean goes to bars and tries to find out how many free drinks he can get just by smiling at the right people.

He gets a little drunker than expected, more successful than he thought he would be. Being drunk makes him way hornier than he already was, so he invites the next guy who buys him a drink to the bathroom with him and the guy licks at his ass until Dean thinks he can see heaven.

The guy has a wife and he tells Dean they're big believers in sharing, so Dean follows him up to his hotel room not that far away and meets the wife. She's already wearing a strap on and the sexiest set of lingerie Dean has ever seen and she takes her time fingering him open before she pushes the strap-on in. She's good, knows exactly how to angle her thrusts to make him see stars, probably has had a lot of practice with her husband already. 

Her husband and her take turns with him. Then, while he is fucking Dean, gentle rocking motions that somehow take more out of Dean than hard fast thrusts do, she slips a lubed finger into his ass along her husband's cock, then another. She's so good at this, stretches him efficiently without any of the burn.

It takes his fucked out brain a little to catch on, but when he does he almost comes. They're both gonna fuck him at the same time. This is the best night of his life.

They're so gentle and sweet, give him plenty of time to adjust and to soothe him as tears spill down his cheeks when they've both bottomed out. At the same time, his cock is dribbling pre-come almost non-stop.

Dean sobs as they fuck him and pet him and worship him, telling him he's so good, so beautiful.

His orgasm seems to drag on forever. He feels stretched thin and worn out, but they bring him back so well, make sure he has time to come down.

He lays between them, just drifting for a while. Once he's feeling lighter, less overwhelmed, he gets out of there. Having fun with a married couple is hot, being the third wheel in their lovey-dovey cuddling, not so much.

They started pretty early, and it's only two am when Dean gets back to his and Sam's motel room.

He enters quietly, but there's no way Sam didn't hear him.

Still, the sounds coming from Sam's bed are unmistakable. He's jerking off.

Dean doesn't really think about it, just kicks off his shoes and pads over to Sam's bed. He crawls under the covers. That's how this works. They don't look at each other. They don't acknowledge each other.

Even in the dark under the sheet, it's easy to find Sam's cock.

He grabs it and gently sucks at the tip. Sammy's hips jerk, but he stays quiet, even when Dean sucks him down to the root in one go. He does this a lot, knows how good at this he is.

It's the first time he sucks a cock as big as Sam's, but the technique stays the same. He thought Sam'd be a gentleman, but he keeps thrusting up his hips, little motions like he can't help himself. Dean tries to encourage him by pressing his nose all the way in Sammy's pubes and holding still, then pushing at Sammy's hips.

Sam finally gets the hint after a couple of tries and starts thrusting, a little more careful than Dean likes but still good. He stays quiet even as he fucks Dean's throat. Stays quiet even as Dean uses all his best tricks, sallowing around Sam, gagging a little and humming to give him some more friction. Stays quiet even as he comes down Dean's throat and Dean swallows all of it. 

Dean pushes away from him enough that they aren't touching anymore, but stays on the bed. They have two kings for once. They definitely didn't pay for them, but if the front desk makes an error like that, Dean isn't going to point it out to them.

For a while there's just quiet. Then Sam reaches for his own cock and Dean realises it's getting hard again. It can't have been more than ten minutes. Dean's night just keeps getting better.

Dean's ass is sore and stretched to the point where he's sort of embarassed about it, and he doesn't know if his cock is going to get hard again anytime soon, but still he sits up to pull off his pants, pushes the sheets away and sits down on Sam's cock, back towards Sam.

He only remembers Sam isn't wearing a condom when he's fully seated on his cock, but Sam doesn't push him off to put on a condom and Dean doesn't want this cock to ever leave his ass, so he assumes it's fine like this.

He carefully pulls off, then sinks back down on Sam's cock. He can hear Sammy's breathing speed up behind him and he does it again, speeding up, trying to angle his back all sexy for Sam's benefit. He feels the slightest brush of Sam's fingertips over his back and hips, then feels the fingers move over his ass to his hole.

Sam clearly noticed how loose Dean is and slips a finger in along his cock. He tugs at Dean's rim while Dean tries to keep up his rythm.

He's so exhausted, but he can feel his cock start to harden again. He fucks himself on his brother's cock, quietly crying out when it hits his oversensitive prostate.

Sam starts to meet Dean's thrusts with thrusts of his own. The more tired Dean gets, the more energy Sam seems to gain.

Eventually Dean just holds still while Sam holds him up off the bed, panting near Dean's back, and thrusts into Dean in short, fast strokes.

Once that position gets uncomfortable, he picks Dean up, holding him closer than he ever has while fucking, gets his legs under him and gets on his knees, still inside Dean. Once he lets go, Dean falls flat onto the mattress, legs spread around Sam's knees. His baby brother fucks him hard and fast, shaking the bed. He puts one forearm over Dean's shoulderblades, pressing him deep into the mattress.

It's not right. It's not something Sammy is supposed to do to him, but it feels so good, so perfect, that he doesn't really care.

His cock is rock hard now, the friction of it being dragged across the sheets with every thrust unbearable. Everything hurts in the best way possible, and Sammy is right there above him to make it even better.

Dean lets out a whimper when Sam pushes in his thumb along with his dick and Sam just holds it there as he fucks Dean. Dean thinks he's going crazy with how turned on he is, how hot it is to have his Sammy so close to him, inside of him.

He comes when Sam pushes in his other thumb and the sound he makes pushes Sam over the edge, too.

For a moment they stay like that, panting hard, Sam still holding Dean down.

Dean pretty much falls asleep before Sammy even pulls out.

The next time he wakes up, he's under the covers and Sam is asleep in the other bed. It's okay, though. He can still feel Sammy's come inside of him.

 

4.

They're on a hunt in North Carolina, and the weather is shit, but at the bar Dean goes to, there's a beautiful woman who tells him she'll fuck him with a strap-on. It's always worth going through shitty weather for a beautiful woman with a strap-on.

She's sweet, yet demanding, praises him whenever he does something right, slaps him hard when he doesn't. The strap-on isn't small. Pretty much Sam-sized. Just the look of it makes his mouth water.

She likes it when he sucks on the dildo, likes it even better when he lets her push his head down onto it. She loves it most when he pretends to struggle with the size of it, when he makes himself gag around it for show.

While he sucks on it, she pinches his nipples, scratches over his abdomen and his thighs, bites the insides of his elbows, his neck, his earlobes. He's so fucking keyed up that he could come if she just touched his cock right now. And then she pushes him down onto the strap-on and doesn't let him up for air and she has to squeeze the base of his cock to keep him from actually coming.

'Such a pretty one,' she says and she gently lets him up and wipes the spit from his chin.

She fucks him open with two of her fingers, mainly to spread the lube around. He knows she's keeping the worst part of the stretch for when she's sinking the actual strap-on into him. She's a fucking genius.

She presses his head into the mattress, ass in the air and slowly but relentlessly pushes into him.

He lets out an embarrassing, dragged out keen and she gives his ass a couple of slaps, making him clench around the already huge dildo. He can't keep quiet, just whimpers and moans and cries out and groans and mumbles all kind of incoherent shit as she rocks her hips, pushing in deeper and deeper. She's not fast, but her thrusts are unpredictable and aimed so perfectly at his prostate it's scary. He keeps making so many different sounds, can't focus enough to stop himself and she slaps his ass again. He keeps clenching and unclenching around the dildo because it hurts so beautifully and she keeps slapping him and biting at his neck and his nipples and he's so fucking close but she won't let him come, lets him come down every time he gets close.

She has one hand squeezed around his neck, the other on her clit and she's rocking her hips in a way that's more pleasurable for her than it is for him. Once she comes, she pulls out, and it really shouldn't be this hot to him that she didn't let him come, that she just used him for her own pleasure without letting him have anything in return.

She's taking off the strap-on and putting her earrings back on when she says it. 'I don't know what they will love more in Hell.' Her eyes flicker black, all-over demon black, and he jerks back. Bad, bad, bad. This is why he wasn't supposed to fuck around. 'That I fucked you or that I killed you.'

'No,' he mumbles. 'Come on, no.' Just his fucking luck. Best lay of the century is a fucking demon.

She's arrogant, though, didn't even take any of his knives. He easily grabs Ruby's off the floor by his pants. He's lucky Sam makes him carry it around whenever he goes out on his own. Shit like this really happens too often.

A man comes out of the door behind the woman, just in time to see her die. He's up next, and then it turns out there's a bunch more demons to come. Reinforcements, maybe, but more likely friends she wanted to share the fun with.

Dean fights his way through. They must have been low-level demons, because even though they leave him with a couple of cuts and a definitely bruised rib, he's still standing and none of them are.

He puts his clothes back on, drives back to the hotel.

'Dean?' Sam gets up from his laptop right away, eyes roaming over his body for anything that can explain the light splatter of blood across his face. There's definitely some of his own blood on him, but he's pretty sure most of it isn't his. It's definitely not as bad as it looks. Nothing that can't wait.

Dean knows that it's bright daylight, that this isn't how it works. They're not supposed to look at each other.

Still he takes off his clothes, and Sam only makes more worried noises when he sees the rest of Dean is lightly covered in blood, too. He repeats Dean's name like it matters, but Dean can worry about injuries later. That's not what he needs to do right now.

'Come on,' Dean says and it's not right. They're not supposed to acknowledge each other. 'Fuck me. Come on.'

There's a moment where nothing happens. Then Sam reaches for his ass, to check if they need lube. They don't. He doesn't go to get a condom, either.

He sinks to his knees, pulling Dean down with him. Dean goes easily, even when Sam gets him to lie down on the floor, flat on his belly. Sammy straddles his thighs, pulls out his cock and fucks into him with a grunt. His pace is steady. Not as punishing as it could be. That's fine. Dean's body hurts way too much to be able to handle being shoved around like that right now.

What he does want, what he has wanted since the demon made him realise how much he loves it, is Sammy's hand around his neck, so he reaches behind himself. They're not supposed to acknowledge each other, but he grabs Sammy's hand, drags it to his throat. Folds his own hand over it and squeezes.

Sam gets the hint. He leans further over Dean, until they're paralell to each other, Sam's chest not quite touching his back, but Sam's head close enough to his for Sam to monitor his breathing.

Then he squeezes down, confidently, as if he's done this before, knows exactly how much pressure to apply to cut off Dean's breath without causing any damage.

Dean's cock is leaking like crazy. He's wheezing whenever Sam lets go enough for him to squeeze a little air through his windpipe. Sammy fucks him hard and good, keeps him seeing black spots, but doesn't let him lose consciousness. Over the blood roaring in his ears, he can hear his brother panting.

Then he lets go of Dean's neck and the oxygen and Sammy nailing his prostrate with each thrust and his whole body feeling like it's flying have him coming, hard and dragged out and perfect.

Sam fucks him through it and comes inside Dean and it feels so good, to get up after trying to fall asleep on the floor but being pulled off by Sam -who's already zipped up his pants and doesn't look like he just had mind-blowing sex at all - and to feel Sam's come running down his thigh.

-

Dean tells him about the demons who attacked him later, and although Dean doesn't mention the sexy times, it's not hard to put two and two together.

 

5.

Dean decides not to have random fucks anymore. It's clearly dangerous and it's not necessary and being unnecessarily dangerous is not something he's supposed to do. Or at least that's what he decides right after last time.

A month later, horny out of his mind, he feels like that descision was made in the heat of the moment, with him still having the blood on him and all, and that it disregarded the very important fact that hot, rough sex actually _is_ completely necessary for him.

So he goes out to a bar, somehow gets lucky on the first try. There's a hot guy at the pool table who looks at him just right. He buys him a drink and his friends leer at the man, but none of them seem surprised.

Once he finishes his game, he comes up to Dean by the bar. 'Wanna get out of here?', he asks. The nice suit and the confident smile and the pretty face are all promising.

'Would love to,' Dean says. 'Any of your friends wanna come along?'

And this must be his lucky fucking day because the guy isn't annoyed or shocked or anything, just grins and goes over to the pool table while Dean pays for the two drinks he's had.

They're surprisingly gentle for a bunch of lawyer-looking types. He'd expect them to be all nice and reserved and then be frustrated and kinky as hell in the sack, but the strip him gently and take their time prepping him and check in with him to see if he's okay with everything they do.

There's six of them in total. He likes the one who immediately wants to fuck his mouth best.

They're at the apartment of one of them. They settle him on the bed on his back, head hanging over the edge, knees pulled up.

The guy who must totally have an oral fixation is already gently cradling Dean's head while the others suck at his skin and push fingers into his ass.

He grins at the man, reaching up to unbuckle and unzip his pants, everything upside down from this position. The guy's cock is probably as long as Sam's, even though it isn't as thick.

Dean licks at it, keeping his eyes directed at the man's face, because he knows that always drives people crazy.

Meanwhile someone is pushing a second finger into his ass, someone else biting and sucking at the skin of his abdomen.

They hunted a sex god once. The being was a total rapist, using their powers to make people want them, but Dean sort of feels like that anyway, without all the mind-altering and rape.

These guys are here for him, worshipping him, want no one but him.

He opens up his mouth for Oral Fixation Guy, but thinks better of it and first says, 'you can fuck my throat. I want you -' he can't hold back a yelp when the person fingering him hits his prostrate hard. 'I want you to fuck my throat. I can take it.'

He mouths at the guy's cock as the guy nods, then just lies back, opens his mouth and waits.

The guy angles his dick with one hand, resting the other on Dean's jaw as he lines himself up and slowly pushes in. Before Dean knows it, the guy's balls are pressing against his nose. The guy gasps above him and experimentally rocks his hips. He finds a rythm that he occasionally interrupts to let Dean breathe. He feels so good, so wordshipped as the guy lets out reverend little gasps and moans, stroking Dean's throat where it's bulging with every thrust.

He can be so good, wants to be so good for them. Wants them to tell him how good he is.

He's so focused on the cock in his mouth that he's completely taken by surprise when someone pushes into his ass.

Maybe it's on purpose, maybe it's dumb luck, but the guy fucking into him hits his prostate on the first try. 

His back arches off the bed as his cock spurts come all over his abdomen. The guys pet him and delight in how responsive he is while the guy in his ass keeps going, nailing his prostate like it's a fucking competition, forcing more beads of come out of Dean's dick.

Dean can't handle it, the perfect pleasure of riding out his orgasm, only made better by the pain of oversensitivity.

He's too far gone to remember breathing and relaxing techniques and he gags around the cock in his throat. The guy's hips stutter before he carefully pulls out, probably as turned on by Dean's spluttering at Dean himself is.

'No,' he says, voice hoarse. 'Don't stop. Want to choke on you.'

'Breathe first,' the guy tells him, stroking his hair and his face, even though spit has dripped down it. 

His ass feels numb and electric at the same time. It only feels better knowing that there's at least four more guys to come after this one. He's gonna be so sore, so fucked out. 

'Ready?' Oral Guy asks and Dean nods, opening up his mouth again. As if he's ever not ready to suck cock.

The guy pushes in again and Dean tries not to freak him out by gagging again. He stays focused and relaxes his throat like he should, taking the guy's lenght without any problems.

The guy in his ass finishes with a couple of hard, stuttering strokes and another takes his place. Not much bigger than the first, but rougher. He grabs Dean's thighs in a bruising hold, fucks into him hard enough to actually hurt. It's perfect, absolutely perfect, and the fucking distracts him again, enough for him to gag around the cock in his mouth.

This time Oral Guy only pulls out far enough that Dean can get a couple of breaths in through his nose, as he's been doing the whole time.

He grabs one of Deans hands and sets it againt his thigh, the _push me away if you need to_ clear even without words.

Then he pushes back into Dean's throat. His stamina is impressive. Even when Dean gags and chokes around his cock, something that, judging from how erratic the guy's thrusts get, really fucking turns him on, he still doesn't come.

Dean feels so good like this. This is the exact place he wants to be forever. Full and taken care of and perfect.

The guy in his ass comes and is replaced by another guy. His cock is wide enough that Dean's eyes tear up (or tear up again, having a cock all the way down his throat is what caused it the first time)

He pushes at Oral Guy's thigh and he immediately pulls out. Dean whimpers against his thigh, his other hand clenched in the bedsheets as his ass adjusts the the girth.

He keens when the guy starts moving. Every nerve in his body feels lit up with how oversensitive he is. To his surprise, his cock is hard again. He's pretty sure right now, he could come from someone just flicking at the sensitive part of his throat.

He paws at Oral Guy's ass to get him to push in again and it's so relieving when he does. He's gentle, but Dean still gags more than he actually sucks, making obscene sounds that shouldn't turn himself on as much as they do.

He moans and whines around the cock in his mouth, coming a second time when someone bites his nipple at the same time the guy fucking his ass hits his prostate.

His back arches and he chokes on the cock in his throat and this is everything he ever wanted.

The guy in his ass comes from Dean clenching around him in the aftermath of his orgasm and someone else takes his place. This guy doesn't fuck him right away, just pushes four fingers it, seems almost in awe at how easily Dean takes them.

Oral Guy has pulled out to let Dean catch his breath and Dean thinks he wants to say something, but nothing coherent comes out. He just wants to be full and used. Nothing else matters.

Oral Guy and the new guy fucking his ass push in at the same time and Dean's limp cock gives a twtich. Someone starts to play with it, mouthing it and rubbing it in a way that hurts so beautifully.

He loves this, loves having so much room inside himself for other people.

Oral Guy's hips stutter and he holds still inside Dean's throat, not letting him breathe, making everything even better. He comes and Dean swallows all of it, even if it would have been hot to have come dripping down his face along with all of the spit.

Dean's own orgasm crashes down on him out of nowhere in time with Oral Guy's.

The guy fucking his ass pulls out and they reposition him to lie on his back. Oral Guy stays by his head, pets his hair and wipes some of the spit out of his eyes.

Dean sucks two of his fingers into his mouth while someone pushes back into his ass.

They fuck him and fuck him and fuck him, and Dean is an incoherent mess. So happy this is happening, so happy it isn't ending. 

Three of them manage to go a second time and Dean whines and whimpers as they fuck him hard. He's being so good for them, he wants them to say it because he knows he's being good, being perfect.

He holds Oral Guy's cock in his mouth because even when soft, it's still enough for him to choke on.

Once everyone is done, someone sets to work massaging his prostate, pushing droplets of come out of his cock even after three orgasms.

They kiss him and pet him and let him drift off, fingers still in his ass, soft cock still in his mouth.

It doesn't take him as long as it should to recover. After napping for half an hour, surrounded by hot guys, he's steady enough to pull on his clothes and drive back to the motel.

Sam looks up from where he was pacing next to his bed when Dean comes into their room.

'You can't go off like that!', Sam bursts out immediately. 'We both know what happened last time.'

'What?'

'What if the person fucking you this time was a shapeshifter or a vampire or a demon again? They could have killed you, Dean. They could have raped you.'

'They didn't.'

'This is dangerous. You need to stop. Seriously.'

'I know, I know. I'm not gonna do it anymore. This was the last time.'

Sam doesn't argue further, just sits down on his bed and puts his laptop in his lap.

Dean sees it, though, before Sam can hide it behind his laptop. He's hard in his jeans, probably, hopefully, from how Dean's lips are all puffy and his lashes are clinging together and his hair is tousled and his voice is hoarse and he walks with a slight limp.

'Sammy,' he mumbles, coming to stand in front if Sam. He likes the way Sam has to look up at him for once. 'Wanna know something?'

Sam just swallows and waits.

'I just got fucked by six guys. One of them fucked my throat. Held out even longer than you always do, just kept going and going while I choked on it. Couldn't fucking breathe, Sammy, just choked on his cock like I should. The others took turns with my ass. Over and over. Got fucked eight times. Was so good for them, Sammy. I took it all. Hurt so good.'

He kicks off his shoes while he speaks, pushes down his pants and steps out of them.

Sammy stays very still, eyes still on Dean's face. He swallows again.

'Wish they hadn't worn condoms, wish you could see my sloppy ass dripping with all their loads. I'm so loose, Sammy. One of them had a cock like a baseball bat. Should have fucked me with a baseball bat. I could take it. I could take a baseball bat for you, Sammy, 'd free up my mouth for your cock. Choke on it. Please-' 

Sam's body collides with his almost painfully. They hit the wall behind Dean and Sammy lifts him up, pushes into him while Dean wails and moans and cries out. He didn't even see him get his dick out.

Sam is holding him up, Dean's legs around his waist, and he fucks Dean with deep, grinding strokes. Not even two minutes and he buries his face in Dean's neck as he comes.

Sam pulls out and carries Dean to his bed to lay him l down and tuck him in. Dean shouldn't be surprised that Sam ignores how Dean tries to tug him into bed with him and goes to sleep in the other bed. 

Dean turns over on his belly so Sammy's come doesn't drip out of him.

 

_And one time_

So Dean promises himself again, no more one night stands, and regrets it again a couple of weeks later.

He's been jerking off every private moment he gets, but it's not working. He doesn't need the orgasm per se. He needs someone else filling him, taking him. He needs to be fucked.

He drinks more in an attempt to forget about it, but that doesn't really help either and makes Sam give him his best lost puppy look. Porn only makes him jealous of whoever is getting it good in the video.

He thinks of buying a dildo, but he's not that desperate yet.

So he focuses on hunting, looks for next cases before they've even cracked the current one. He keeps dreaming of Sammy fucking him, holding him down and he's pretty sure it'd stop if he could just get it out of his system.

He's debating proposing to Sam some once per month rule, or just going behind Sam's back next chance he has. He can do both. Get fucked with Sam's permission once a month and go behind his back the rest of the time.

'You got a minute?', Sam asks when he's just back from the gym, hair still wet from the shower.

Dean is lying on his bed watching TV, so he sits up, turns off the TV and nods at Same to go on.

'You're... I'm sorry if this is difficult for you, the no one night stands thing.'

Dean doesn't really know what to say to that and hopes Sammy is going somewhere with this, because it's pretty shitty as an independent statement.

'I thought maybe... I understand that you have needs, but it's just too dangerous - so I figured.' He falls silent for a moment, then takes a deep breath and pushes on. 'I could help out, whenever you need it.'

'Help out?' Dean thinks he knows what he's saying, but he doesn't want to get his hopes up. They don't acknowledge each other. They don't look at each other. They definitely don't talk about fucking in broad daylight, when they're not even about to do something.

'You know what I mean.'

'Yeah. No need, though, Sammy. I'll be fine. No heroic sacrifice needed from you for once.'

'It wouldn't -' Sam starts, but he seems to think better of it and turns away from Dean slightly. 'Of course,' he says instead. 'Just - you've been doing great so far, with the not sleeping around thing, but I know how hard it is and I wanted you to have a safe option, if you ever need it.'

'Thanks, Sam,' he manages, mouth dry for some reason.

'I'm going to the store, you need anything?', Sam asks and just like that they're off thin ice and back to a normal conversation.

-

Sam doesn't bring it up again. Dean keeps masturbating whenever he can and tries to convince himself it's enough. He looks up dildo's online but doesn't buy any.

It's been a week since Sam's proposal and well over a month since the last time Dean has had sex. It makes him feel more lonely than he expected. He'd thought sex was something purely physical for him, but he misses the comfort of it, the closeness to another human being.

Their current motel only has one kingsize bed. Sharing a bed, especially a big one that has enough room for them both to sleep comfortably without touching, has never been a big deal to them. Dean likes having a bed for himself mostly because he's never really had a lot more than a motel room bed that he didn't have to share with his brother and his dad. He doesn't mind sharing that much, though. He's so used to it with Sam. There's nothing weird about it anymore, there never was.

Except now, after an exhausting salt and burn, neither of them is asleep and Dean can feel the sheets moving as Sam strokes up and down his own cock.

He knows what he's supposed to do, so that's exactly what he does. He doesn't acknowledge Sam, doesn't look at him, but reaches over and pushes Sammy's hand away so Dean can stroke his baby brother's cock.

Sam is quiet as always, but he thrusts up into Dean's hand and pulls Dean towards him so he can thrust against his leg, adding to the friction. Dean is so turned on by how easily Sam manhandles him, using his other hand to squeeze his own cock.

Sam pushes him on his back and pulls Dean's hand away from Dean's cock. It's dark, but they're definitely looking at each other now. 

Sam comes to hang over him and reaches down to prod at Dean's dry hole. Dean moans and whimpers, knowing that it's the best way to make Sam lose control. He sort of wants Sam to fuck into his unprepped hole just like that, wants to be owned by his brother as toroughly as possible.

Sam gets lube from under his pillow, though, and it occurs to Dean that he planned ahead for the lube to be there, but he loses that train of thought when Sammy's dry index finger pushes past his rim.

Dean gasps and lets out high pitched moans as Sammy drags the finger in and out of him. Then he pulls out, lubes up two fingers and pushes them in, stretching Dean fast enough that it hurts a little, jabbing at his prostate when Dean gets too quiet for his liking.

Sam pulls out his fingers once Dean can comfortably fit three, which isn't exactly enough of a stretch to prepare him for Sam's cock. Dean has always been saying that his baby brother is a genius, but he wants to reiterate that now. Sam is so fucking amazing, leaving part of the stretching for when he's actually pushing his cock into Dean.

Which he does pretty much right then. He sits up on his knees and pulls Dean up to sit in front of him, back to Sam, on his knees, too. Sam guides Dean's hands to the headboard and even though Sam doesn't say anything, Dean knows he's supposed to leave them there.

Sam pushes into him slowly and Dean can't stay quiet, babbling incoherently as his body is stretched to make room for Sammy.

He starts to rock his hips before Dean has compeltely adjusted to his size and it hurts so beautifully. He sets a fast, torough rythm while Dean clings to the headboard and moans with every thrust.

Sam mouths at his back, pinches his skin, squeezes his sides and his arms and his hips until there's red marks ready to turn into bruises all over his body. Dean's body is being jostled around while Sam fucks him and this is perfect, how little control he has in this, how Sam is making all his choices for him.

Then Sammy puts both hands around Dean's throat. He doesn't really squeeze as much as he just uses his grip as leverage to fuck Dean, which leaves Dean little room to breathe. He comes when Sam momentarily squeezes hard enough to cut off his breath and Sam keeps fucking him, coming when Dean starts to whimper from oversensitivity.

He pulls out and lets go of Dean, who falls forward onto the bed. Sam goes to sit back against the headboard and watches Dean, then grabs his chin and guides Dean's head to his soft dick. Dean holds it in his mouth while he catches his breath and Sammy strokes his hair. It can only be a couple of minutes before Sam starts to fill out again, which is just unfair. They share part of their DNA, Dean should be able to do that, too.

Sam cradles Dean's face as he pushes his now fully hard dick further into Dean's mouth, easily pushing into his throat.

Dean lazily sucks at his brother's big cock for a while, until Sammy starts thrusting little by little.

Dean can take it easily, but he makes himself gag around Sam's cock because it's hotter that way. He chokes and splutters as Sam gently fucks in and out of him.

Dean loves this, loves being good. Sam strokes his face and fucks him a little harder, balls slapping against Dean's chin.

This shouldn't make him as happy as it does. Shouldn't make him feel complete in a way only saving lives ever does anymore, shouldn't make him feel like life only makes sense here and now. He shouldn't love this so much because that means he will need it, will depend on it. And depending on things isn't safe.

He can't really think of any reason why that matters, though, why anything matters other than Sammy.

Sam lets out a quiet moan when he comes down Dean's throat, folding over Dean in a way that only pushes him further inside. Dean swallows every drop op Sam's come while Sam moans and strokes his shoulder as he slowly pulls out. Dean just rests his head on his brother's thigh while Sam continues to massage his shoulder.

Dean knows Sam is looking at him and it should worry him more, that they keep breaking their own rules, that this keeps getting further and further out of hand, but he can't bring himself to care when he feels this good.

He strokes Sammy's soft cock as he watches it up close in the dark. It stays soft, hopefully will for at least a little bit, because it's going to be humiliating if his brother can come three times while Dean can only get it up up once in the same time.

Sammy's cock starts to harden again after maybe fifteen minutes and Dean knows he won't take that much longer to be able to get it up again. Or he hopes so, at least.

Sam's hand on his shoulder grabs hold of Dean, gently tugs him upwards.

Dean doesn't make any desicion, just follows Sam's touches until he's seated over Sam's legs, facing Sam, who's still leaning against the headboard.

They're acknowledging each other, they're looking at each other. But it's fine. Everything is still okay. Or at least it feels okay. It feels perfect.

Dean braces himself on Sam's hips and lifts off while Sam lines up his cock. He sinks down in one go. The stretch is still intense, but Dean wants to show Sammy how good he is.

He doesn't give himself time to adjust, just starts bouncing on his brother's cock and moans when Sam bites his nipples.

He starts to jerk his own cock just to get Sam to slap him on the thigh. The sting feels good, so he grabs his cock again, again, again, each time rewarded with a perfectly painful hit.

Sam is fucking up into him and carefully lifts Dean up, staying inside of him as he lays Dean out on his back and comes to hang over him.

Dean whines as Sam slows his thrusts, squirming in an attempt to get anything - more friction, more pain, more, more.

Sam puts his forearm across Dean's collarbones, pushing him down into the mattress.

Then he kisses Dean hard.

Dean doesn't know what to do for a second, his cock instantly hard, his brain short-circuiting.

Sam kisses like he means it, like it's better than fucking breathing and Dean kisses back with a moan. It's another way that Sammy takes control, owns him so perfectly.

Sam starts thrusting again, rythm brutal even while he keeps kissing Dean. Dean reaches up to pull at Sam's hair and Sam lets out a stuttering moan. He starts to kiss and bite Dean's neck while Dean tugs his hair.

Dean comes with Sammy spearing him open and biting down hard above his collarbone.

Sam keeps going, going and going. Dean whines and whimpers, too oversensitive to keep quiet. This is still the part he loves most, the part where Sammy just takes and takes and Dean can do nothing but give.

He gets to the point where it just hurts, no more pleasure left in him, and even that feels so perfect. He tugs at his spent cock and Sam finally comes from the pained whine Dean lets out.

This time he has two of Sammy's loads inside of him and it's better than any other time he's been fucked before.

Sam pulls out and drops down next to Dean. Dean tugs Sammy closer and Sammy nuzzles his neck. It doesn't take them long to fall asleep.


End file.
